The Nef reaction of isocyanides

Fabio La Spisa, Gian Cesare Tron, Laurent El Kaïm

Risultato della ricerca: Contributo su rivistaArticolo di reviewpeer review

Abstract

The interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intraÂ- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef reaction of isocyanides focusing on mechanism and regioselectivity issues. 1 Isocyanide Chemistry 2 Isocyanide Interaction with Acyl Chlorides and Analogues 2.1 General Considerations 2.2 Methods of Preparation of α-Keto Imidoyl Chlorides 2.3 Nef Reaction Mechanism 3 Reactivity of α-Keto Imidoyl Chlorides 3.1 General Behavior of α-Keto Imidoyl Chlorides 3.2 Intramolecular Trappings 3.3 Intermolecular Trappings and Three-Component Reactions 4 Extensions of the Nef Reaction 5 Conclusion

Lingua originaleInglese
Numero di articolo4068
pagine (da-a)829-841
Numero di pagine13
RivistaSynthesis
Volume46
Numero di pubblicazione7
DOI
Stato di pubblicazionePubblicato - apr 2014

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